CN107343968A - A kind of vegatable tannin available for organizational project freezes hydrogel and its preparation method and application - Google Patents
A kind of vegatable tannin available for organizational project freezes hydrogel and its preparation method and application Download PDFInfo
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Abstract
A kind of vegatable tannin available for organizational project freezes hydrogel and its preparation method and application, prepares the vegatable tannin aqueous solution and N, N the DMAA aqueous solution；Crosslinking agent is added after both are mixed；Initiator solution is added in reaction system；Solution is poured into mould, is placed in low-temp reaction kettle and reacts；Mould is taken out from low-temp reaction kettle, can obtain freezing hydrogel after thawing.Operating procedure of the present invention is simple, and implementation condition is gentle, and the chilled water gel biological compatibility of preparation is good, can stick a variety of different types of cells in gel surface.
Description
Technical field
The invention belongs to native biopolymer Material Field that can be medical, and in particular to a kind of available for organizational project
Vegatable tannin freezing hydrogel and its preparation method and application.
Background technology
Hydrogel be as high molecular polymer as obtained from the physical bond of non-covalent bond or covalent chemical crosslinking
Three-dimensional network.Due to there is very high affinity to water, suction can be swelled in water with substantial amounts of hydrophilic radical, hydrogel
Itself tens times of even thousands of times of moisture is received, and with the ability for keeping moisture well, the water under ambient pressure
Point will not also be lost in, environment that can very well in simulation human body, therefore, hydrogel field of tissue engineering technology application with
Its only thick advantage.As tissue engineering material, hydrogel must possess good biocompatibility, mechanical property, cell or
Protein adsorption etc..In addition, the loose structure of continuous uniform is very necessary for tissue engineering module.Highly
Continuously, the controllable loose structure in aperture is advantageous to adhesion, propagation, differentiation and the formation of tissue of cell.Different aperture point
Cloth largely affects vascularization, the transport of cell nutrients and the discharge of products of cellular metabolism.Traditional synthesis class
Macromolecule hydrogel（Such as polyacrylic acid, polyacrylamide, polyacrylate）Possess comparatively ideal mechanical performance, it is controllable
Chemical composition, preparation process and molecular weight, but its biocompatibility is poor, pore structure is excessively fine and close, for external environment condition
Response slowly, lack bioactivity and not degradable, cause system not possess cell recognition signal, be unsuitable for active material and
The load of cell.
Vegatable tannin is universally present in the positions such as the leaf of plant, fruit, root and bark, being important natural polyphenol class
Early and more a kind of compound must be compared by being studied in active material, and natural products.The polyphenol hydroxyl chemistry of vegatable tannin
Structure and unique chemical property make it show with the stronger multiple biological activities such as anti-oxidant, antiviral, antitumor, and
And can be reacted with protein, polysaccharide, alkaloid, with complexing of metal ion, the suppression to bacterium and enzyme, to some crop diseases and pests
Harmful resistance, it is used as bacteriostatic agent, antineoplastic, antioxidant, preservative, tanning extracts, cosmetics, binder, Shui Chu
Manage agent and polymeric adsorbent etc..
The method being used in combination using interpenetrating polymer networks and freezing polymerization, by vegatable tannin and high molecular polymer phase
Fusion, the gel rubber material of preparation can efficiently solve the problem of synthesis family macromolecule hydrogel is present.Interpenetrating polymer networks
It is a kind of simple effective method for preparing organizational project class hydrogel.In system, vegatable tannin is inserted into polymer three-dimensional net
In network, the mutual physical entanglement of strand with network, porous structure is formed, by hydrogen bond equimolecular between the two
Intermolecular forces maintain the stabilization of network structure, and it is high farthest to play high vegatable tannin hydrophily, bacteriostasis and synthesis
The advantages of Molecularly Imprinted Polymer mechanical strength is higher.On the other hand, the gel prepared by freezing polymerization, due to its special polymerization
Mechanism, gel be generally configured with macroporous structure continuous, that hole density is high, contributes to diffusion and the products of cellular metabolism of nutriment
Excretion, the histoorgan in organism is preferably simulated, place is provided for the infiltration of cell, growth diffusion, for tissue growth institute
Nutriment and tissue metabolism's thing offer passage are provided.And the mechanical strength of gel is higher, it can preferably meet that it is being organized
The use of engineering field.Freezing polymerization and interpenetrating polymer networks are used in combination and prepare organizational project class hydrogel, Ke Yitong
Overregulate the conditions such as ratio and the preparation temperature of vegatable tannin and high molecular polymer includes hole density, aperture to loose structure
Scope is controlled by, and significantly reduces the excitant to institute's adherent cell so that cultivating cell can be in the hole of gel
Portion is adhered to and bred.
The content of the invention
The technical problem of solution：The purpose of the present invention is exactly to overcome pore structure existing for synthesis family macromolecule hydrogel
It is excessively fine and close, not degradable and one kind is provided possesses continuous macroporous structure, degradable, biological the defects of lack bioactivity
Good vegatable tannin hydrogel of compatibility and its preparation method and application, this method operating procedure is simple, and implementation condition is gentle.
Technical scheme：A kind of vegatable tannin available for organizational project freezes the preparation method of hydrogel, and step is：（1）
Vegatable tannin powder is dissolved in deionized water, stirred, the mass concentration 1%-3% vegatable tannin aqueous solution is made；（2）
N,N-DMAA is dissolved in deionized water, stirred, 35%-45% N, N- dimethyl allene acyls is made
Amine aqueous solution；（3）The above-mentioned vegatable tannin aqueous solution and the N,N-DMAA aqueous solution are mixed, add friendship
Join agent, be configured to homogeneous solution；The vegatable tannin:N, N- DMAA:The mass ratio of crosslinking agent is（5 ~
15）：（100~ 200）：（12 ~ 36）；（4）Initiator powder is dissolved in deionized water, stirred, it is dense that quality is made
Spend the initiator solution for 2% ~ 4%；The initiator solution of effective dose is added into step（3）In gained reaction system；（5）
By step（4）In solution pour into mould, be placed in low-temp reaction kettle, -10 DEG C ~ -40 DEG C react 10 min ~ 30
min；（6）By step（5）In mould taken out from low-temp reaction kettle, 25 DEG C ~ 35 DEG C melt after can obtain chilled water
Gel.
Above-mentioned vegatable tannin is change fragrant fruit tannin, Chinese chestnut bud tannin or rubber Bowl tannin.
Above-mentioned its mass fraction of the vegatable tannin aqueous solution is 3%.
Its mass fraction of above-mentioned N, N- the DMAA aqueous solution is 35%.
Above-mentioned initiator is water soluble starter such as ammonium persulfate, potassium peroxydisulfate or ammonium ceric nitrate.
Above-mentioned crosslinking agent is the monomer containing unsaturated double-bond, and the crosslinking agent is N, N '-methylene-bisacrylamide,
Two methacrylaldehyde contracting pentaerythrites, diethylene glycol divinyl ether, divinyl -1,4- butanediol etheres, methacrylic acid 2- hydroxyls
Ethyl ester, dimethylaminoethyl methacrylate, dimethylaminoethyl acrylate methyl ammonia ethyl ester, DAAM, four allyloxy second
Alkane or ethylene glycol dimethacrylate.
Vegatable tannin made from the above method freezes hydrogel.
Application of the above-mentioned vegatable tannin freezing hydrogel in tissue engineering material is prepared.
Beneficial effect：（1）The inventive method preparation process is efficient, succinct, environmental protection；The mild condition that technology is implemented, reaction
Time is short；Technology implementing process is simple, product is without through special postprocessing working procedures, being placed in low temperature ring after reaction raw materials are chilled
Border may be polymerized, and polymerization heat easily disperses.（2）Freezing hydrogel prepared by the inventive method, need not in course of reaction
Any auxiliary agent is added, the problem of residual in the absence of pore-foaming agent；（3）The freezing hydrogel prepared using the inventive method has continuous
Loose structure, pore size can by crosslinking agent dosage carry out accuracy controlling；（4）The chilled water prepared using the inventive method
Gel possesses splendid mechanical strength, remains able to restore to the original state when bearing high pressure；（5）Prepared using the inventive method cold
External degradation can efficiently be completed by freezing hydrogel, and degradation rate can carry out accuracy controlling by the dosage of vegatable tannin；（6）Utilize this
Chilled water gel biological compatibility prepared by inventive method is good, can stick a variety of different types of cells in gel surface.
Brief description of the drawings
Fig. 1 is the plastic process schematic of vegatable tannin freezing hydrogel；
Fig. 2 is vegatable tannin freezing hydrogel internal pore structure scanning electron microscope diagram；Wherein a is using 24 mg crosslinking agents
The vegatable tannin freezing hydrogel internal pore structure of preparation, b are that the vegatable tannin prepared using 72 mg crosslinking agents freezes hydrogel
Internal pore structure；
Fig. 3 is vegatable tannin freezing hydrogel stress-strain curve；
Fig. 4 is that vegatable tannin freezing hydrogel is degraded in PBS solution schematic diagram in vitro；Wherein a is using 3% vegatable tannin water
Vegatable tannin freezing hydrogel prepared by solution, b are that the vegatable tannin prepared using the 1% vegatable tannin aqueous solution freezes hydrogel；
Fig. 5 is Chinese hamster ovary cell（Chinese hamster ovary celI）Illustrate in the vegatable tannin chilled water gel entrapment culture growing state of 4 days
Figure.
Embodiment
With reference to specific embodiment, the present invention is described in detail.It should be understood that these embodiments are merely to illustrate this
Invention rather than limitation the scope of the present invention.In addition, it is to be understood that after the content of the invention lectured has been read, this area skill
Art personnel can make various changes or modifications to the present invention, and these equivalent form of values equally fall within the application appended claims institute
The scope of restriction.
Embodiment 1
As shown in figure 1, taking Chinese chestnut bud tannin to add deionized water, magnetic agitation is completely dissolved up to Chinese chestnut bud tannin, is configured to
The Chinese chestnut bud tannin aqueous solution of mass percent concentration 3%.N,N-DMAA is taken to add deionized water, stirring is equal
It is even, the N,N-DMAA aqueous solution of mass percent concentration 35% is made.By two kinds of solution by volume 1:2 ratios
It is placed in after mixing in 0 DEG C of ice bath, is stirred 1 hour in ar gas environment.Add afterwards the methacrylaldehyde contracting pentaerythrites of 24 mg bis- after
Continuous stirring 10 minutes.Take ammonium ceric nitrate to add deionized water, stir, it is water-soluble that the initiator of mass percent concentration 2% is made
Liquid.1 mL initiator solutions are added dropwise with liquid-transfering gun, continue mechanical agitation 10 minutes.This mixed liquor is taken out from ice bath, fallen
Enter in 35 × 50 mm moulds, this mould is placed in low-temp reaction kettle, react 10 min at -40 DEG C.Then by mould
Take out, can obtain freezing hydrogel after under 25 DEG C of environment melting.
Jelly gel sample is placed in freeze drier and is dried, after 48 hours, lyophilized sample is taken out, is cut into small
Block.Then conducting resinl is attached on sample stage, then gel bits are attached on conducting resinl, then gold-plated to improve conductance.Sweeping
The pore structure of observed under electron microscope different parts is retouched, randomly selects the aperture image of gel internal cross section, such as a in Fig. 2
It is shown.From Fig. 2-a, the freezing hydrogel prepared using 24 mg crosslinking agents possesses more obvious pore structure.
The gel that diameter is about 35 mm is cut into the sample that height is about 10 mm, is put into the compression mould of material testing machine
Centre, think that 2 mm/min speed is compressed.Observation freezing hydrogel is in the deformation situation depressed during compression.Compression
After the completion of, with the compression stress of initial cross sectional product calculated for gel, compression strain is calculated as shown in Figure 3 with elemental height
Load-deformation curve.
Lyophilized gel sample is placed in deionized water 3 days, after gel swelling balance, sample is placed in pH's 7.4
In PBS solution, tested under the conditions of 37 DEG C.Sample is taken out within the specified time, the molten of surface is wiped with wet filter paper
Liquid, then weigh.Utilize residual mass percentage calculation formula：Residual mass percentage (%)=specified time gel weight/
Swelling equilibrium gel initial weight × 100, the degradation rate curve as shown in a in Fig. 4 is calculated.From Fig. 4-a, adopt
The chilled water gel degradation speed prepared with 24 mg crosslinking agents is very fast.
The Chinese hamster ovary celI frozen is taken out from -70 DEG C of refrigerators, is thawed rapidly in 37 DEG C of water-baths, addition contains 10% tire ox blood
Clear DMEM culture mediums（Containing 100 U/mL penicillin and 100 μ g/mL streptomysins）Recovery cell.In 37 DEG C, 5% CO2Training
Support and cultivated in case, trypsin digestion and cell and Secondary Culture with 0.25%.Then a diameter of 10 mm is made in gel sample,
Thickness is 2 mm thin slice, is placed in 40%（v/v）Sterilized 12 hours in ethanol solution, then again with 37 DEG C of PBS solution and
DMEM soaked overnights, to remove the ethanol solution of gel surface and inside.Operation is completed in super-clean bench above.Then will
The gel sample of sterilizing tiles into 6 orifice plates, with 1 × 105/cm2Density Chinese hamster ovary celI is inoculated into gel surface, 37 DEG C,
5% CO2Under conditions of cultivate respectively 4 days.Chinese hamster ovary celI will be fixed with 3% glutaraldehyde afterwards.After 10 minutes, with 25 DEG C
PBS solution elution gel sample three times, then in fluorescence microscopy Microscopic observation cell, obtains cell growth feelings as shown in Figure 5
Condition schematic diagram.
Embodiment 2
As shown in figure 1, the fragrant fruit tannin of taking adds deionized water, magnetic agitation is completely dissolved up to tannin, is configured to quality hundred
Divide the Chinese chestnut bud tannin aqueous solution of specific concentration 3%.Take N,N-DMAA to add deionized water, stir, be made
Mass percent concentration 35% N, N- the DMAA aqueous solution.By two kinds of solution by volume 1:The mixing of 2 ratios is rearmounted
In 0 DEG C of ice bath, stirred 1 hour in ar gas environment.The methacrylaldehyde contracting pentaerythrites of 72 mg bis- are added afterwards continues stirring 10
Minute.Take ammonium ceric nitrate to add deionized water, stir, the initiator solution of mass percent concentration 2% is made.Use liquid relief
1 mL initiator solutions are added dropwise in rifle, continue mechanical agitation 10 minutes.This mixed liquor is taken out from ice bath, pour into 35 ×
In 50 mm moulds, this mould is placed in low-temp reaction kettle, reacts 10 min at -40 DEG C.Then mould is taken out, 25
It can obtain freezing hydrogel after under DEG C environment melting.
Jelly gel sample is placed in freeze drier and is dried, after 48 hours, lyophilized sample is taken out, is cut into small
Block.Then conducting resinl is attached on sample stage, then gel bits are attached on conducting resinl, then gold-plated to improve conductance.Sweeping
The pore structure of observed under electron microscope different parts is retouched, randomly selects the aperture image of gel internal cross section, such as b in Fig. 2
It is shown.From Fig. 2-b, the pore structure of the freezing hydrogel prepared using 72 mg crosslinking agents is more fine and close.
Embodiment 3
As shown in figure 1, taking Chinese chestnut bud tannin to add deionized water, magnetic agitation is completely dissolved up to Chinese chestnut bud tannin, is configured to
The Chinese chestnut bud tannin aqueous solution of mass percent concentration 1%.N,N-DMAA is taken to add deionized water, stirring is equal
It is even, the N,N-DMAA aqueous solution of mass percent concentration 35% is made.By two kinds of solution by volume 1:2 ratios
It is placed in after mixing in 0 DEG C of ice bath, is stirred 1 hour in ar gas environment.Add afterwards the methacrylaldehyde contracting pentaerythrites of 24 mg bis- after
Continuous stirring 10 minutes.Take ammonium ceric nitrate to add deionized water, stir, it is water-soluble that the initiator of mass percent concentration 2% is made
Liquid.1 mL initiator solutions are added dropwise with liquid-transfering gun, continue mechanical agitation 10 minutes.This mixed liquor is taken out from ice bath, fallen
Enter in 35 × 50 mm moulds, this mould is placed in low-temp reaction kettle, react 10 min at -40 DEG C.Then by mould
Take out, can obtain freezing hydrogel after under 25 DEG C of environment melting.
Lyophilized gel sample is placed in deionized water 3 days, after gel swelling balance, sample is placed in pH's 7.4
In PBS solution, tested under the conditions of 37 DEG C.Sample is taken out within the specified time, the molten of surface is wiped with wet filter paper
Liquid, then weigh.Utilize residual mass percentage calculation formula：Residual mass percentage (%)=specified time gel weight/
Swelling equilibrium gel initial weight × 100, the degradation rate curve as shown in b in Fig. 4 is calculated.
Claims (8)
1. a kind of vegatable tannin available for organizational project freezes the preparation method of hydrogel, it is characterised in that step is：
（1）Vegatable tannin powder is dissolved in deionized water, stirred, mass concentration 1%-3% vegatable tannin water is made
Solution；
（2）N,N-DMAA is dissolved in deionized water, stirred, 35%-45% N, N- diformazans is made
Base acrylamide aqueous solution；
（3）The above-mentioned vegatable tannin aqueous solution and the N,N-DMAA aqueous solution are mixed, add crosslinking agent,
It is configured to homogeneous solution；The vegatable tannin:N, N- DMAA:The mass ratio of crosslinking agent is（5 ~ 15）：（100
~ 200）：（12 ~ 36）；
（4）Initiator powder is dissolved in deionized water, stirred, the initiator water that mass concentration is 2% ~ 4% is made
Solution；The initiator solution of effective dose is added into step（3）In gained reaction system；
（5）By step（4）In solution pour into mould, be placed in low-temp reaction kettle, -10 DEG C ~ -40 DEG C react 10
min ~ 30 min；
（6）By step（5）In mould taken out from low-temp reaction kettle, 25 DEG C ~ 35 DEG C melt after can obtain chilled water
Gel.
2. the preparation method according to claim 1 available for organizational project vegatable tannin freezing hydrogel, its feature exists
It is to change fragrant fruit tannin, Chinese chestnut bud tannin or rubber Bowl tannin in the vegatable tannin.
3. the preparation method according to claim 1 available for organizational project vegatable tannin freezing hydrogel, its feature exists
In described its mass fraction of the vegatable tannin aqueous solution be 3%.
4. the preparation method according to claim 1 available for organizational project vegatable tannin freezing hydrogel, its feature exists
In the N, its mass fraction of the N- DMAAs aqueous solution is 35%.
5. the preparation method according to claim 1 available for organizational project vegatable tannin freezing hydrogel, its feature exists
In the initiator be water soluble starter such as ammonium persulfate, potassium peroxydisulfate or ammonium ceric nitrate.
6. the preparation method according to claim 1 available for organizational project vegatable tannin freezing hydrogel, its feature exists
It is the monomer containing unsaturated double-bond in the crosslinking agent, the crosslinking agent is N, N '-methylene-bisacrylamide, two propylene
Aldehyde contracting pentaerythrite, diethylene glycol divinyl ether, divinyl -1,4- butanediol etheres, 2-hydroxyethyl methacrylate, first
Base dimethylaminoethyl acrylate, dimethylaminoethyl acrylate methyl ammonia ethyl ester, DAAM, tetraallyloxyethane or second two
Alcohol dimethylacrylate.
7. vegatable tannin made from any methods described of claim 1 ~ 6 freezes hydrogel.
8. application of the vegatable tannin freezing hydrogel in tissue engineering material is prepared described in claim 7.
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Cited By (3)
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| CN109331216A (en) * | 2018-11-28 | 2019-02-15 | 福建师范大学 | A kind of quick-acting haemostatic powder hydrogel and preparation method thereof |
| CN110604126A (en) * | 2018-06-14 | 2019-12-24 | 宁波化奇工程技术有限公司 | Non-formaldehyde environment-friendly pathological tissue fixing agent |
| CN114230811A (en) * | 2021-11-23 | 2022-03-25 | 中国林业科学研究院林产化学工业研究所 | Broussonetia papyrifera leaf protein hydrogel used as cell carrier and preparation method and application thereof |
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| CN110604126A (en) * | 2018-06-14 | 2019-12-24 | 宁波化奇工程技术有限公司 | Non-formaldehyde environment-friendly pathological tissue fixing agent |
| CN109331216A (en) * | 2018-11-28 | 2019-02-15 | 福建师范大学 | A kind of quick-acting haemostatic powder hydrogel and preparation method thereof |
| CN109331216B (en) * | 2018-11-28 | 2021-03-30 | 福建师范大学 | Quick hemostatic hydrogel and preparation method thereof |
| CN114230811A (en) * | 2021-11-23 | 2022-03-25 | 中国林业科学研究院林产化学工业研究所 | Broussonetia papyrifera leaf protein hydrogel used as cell carrier and preparation method and application thereof |
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Application publication date: 20171114 |